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Volume 69 
Part 9 
Page o1451  
September 2013  

Received 12 August 2013
Accepted 15 August 2013
Online 17 August 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.002 Å
R = 0.045
wR = 0.143
Data-to-parameter ratio = 22.1
Details
Open access

3-Benzyl-1-{[3-(4-chlorophenyl)isoxazol-5-yl]methyl}-1H-benzimidazol-2(3H)-one

aLaboratoire de Chimie Organique Appliquée, Université Sidi Mohamed Ben Abdallah, Faculté des Sciences et Techniques, Route d'Immouzzer, BP 2202 Fès, Morocco,bUnité de Catalyse et de Chimie du Solide (UCCS), UMR 8181, Ecole Nationale Supérieure de Chimie de Lille, France,cUSR 3290 Miniaturisation pour l'Analyse, la Synthèse et la Protéomique, 59655 Villeneuve d'Ascq Cedex, Université Lille 1, France, and dLaboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V-Agdal, Avenue Ibn Battouta, BP 1014, Rabat, Morocco
Correspondence e-mail: amal_haoudi@yahoo.fr

In the title compound, C24H18ClN3O2, the benzimidazole plane is nearly perpendicular to the phenyl ring and to the isoxazole ring, making dihedral angles of 75.95 (7) and 73.04 (8)°, respectively, but the two residues point in opposite directions with respect to the benzimidazole plane. The dihedral angle between the chlorophenyl and isoxazole rings is 7.95 (8)°. In the crystal, molecules are linked by pairs of C-H...O hydrogen bonds into inversion dimers.

Related literature

For the biological activity of isoxazoline derivatives, see: Sakuma et al. (2011[Sakuma, S., Endo, T., Nakamura, H., Yamazaki, S. & Yamakawa, T. (2011). Bioorg. Med. Chem. Lett. 21, 240-244.]); Hu et al. (2010[Hu, D., Liu, S., Huang, T., Tu, H., Li, W., Zhu, X. & Zhang, A. (2010). Chin. J. Org. Chem. 30, 1366-1371.]); Wang et al. (2010[Wang, S., Yan, J., Chen, J., Zhang, T., Zhao, Y. & Xue, M. (2010). Eur. J. Med. Chem. 45, 2663-2670.]). For benzimidazol-2-one derivatives, see: Belaziz et al. (2012[Belaziz, D., Kandri Rodi, Y., Ouazzani Chahdi, F., Essassi, E. M., Saadi, M. & El Ammari, L. (2012). Acta Cryst. E68, o3069.]).

[Scheme 1]

Experimental

Crystal data
  • C24H18ClN3O2

  • Mr = 415.86

  • Triclinic, [P \overline 1]

  • a = 8.5427 (2) Å

  • b = 9.8290 (2) Å

  • c = 13.2658 (3) Å

  • [alpha] = 81.133 (1)°

  • [beta] = 78.763 (1)°

  • [gamma] = 64.343 (1)°

  • V = 981.73 (4) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.22 mm-1

  • T = 296 K

  • 0.60 × 0.39 × 0.13 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.688, Tmax = 0.746

  • 70806 measured reflections

  • 5994 independent reflections

  • 4622 reflections with I > 2[sigma](I)

  • Rint = 0.029

Refinement
  • R[F2 > 2[sigma](F2)] = 0.045

  • wR(F2) = 0.143

  • S = 1.03

  • 5994 reflections

  • 271 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.55 e Å-3

  • [Delta][rho]min = -0.35 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C20-H20...O2i 0.93 2.53 3.1949 (19) 129
Symmetry code: (i) -x+1, -y+2, -z+1.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT-Plus (Bruker, 2009[Bruker (2009). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT6928 ).


References

Belaziz, D., Kandri Rodi, Y., Ouazzani Chahdi, F., Essassi, E. M., Saadi, M. & El Ammari, L. (2012). Acta Cryst. E68, o3069.  [CSD] [CrossRef] [details]
Bruker (2009). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Hu, D., Liu, S., Huang, T., Tu, H., Li, W., Zhu, X. & Zhang, A. (2010). Chin. J. Org. Chem. 30, 1366-1371.  [ChemPort]
Sakuma, S., Endo, T., Nakamura, H., Yamazaki, S. & Yamakawa, T. (2011). Bioorg. Med. Chem. Lett. 21, 240-244.  [CrossRef] [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]
Wang, S., Yan, J., Chen, J., Zhang, T., Zhao, Y. & Xue, M. (2010). Eur. J. Med. Chem. 45, 2663-2670.  [ISI] [CrossRef] [ChemPort] [PubMed]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o1451  [ doi:10.1107/S160053681302299X ]

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